Enantioselective N-heterocyclic carbene catalyzed formal [3+2] cycloaddition using α-aroyloxyaldehydes and oxaziridines |
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Authors: | Ryan WF Kerr Mark D Greenhalgh Alexandra MZ Slawin Polly L Arnold Andrew D Smith |
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Institution: | 1. EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews KY16 9ST, UK;2. EaStCHEM School of Chemistry, The University of Edinburgh, David Brewster Road, Edinburgh EH9 3FJ, UK |
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Abstract: | An enantioselective N-heterocyclic carbene catalysed formal 3+2] cycloaddition has been developed for the synthesis of oxazolindin-4-one products. The reaction of oxaziridines and α-aroyloxyaldehydes under N-heterocyclic carbene catalysis provides the formal cycloaddition products with excellent control of the diastereo- and enantioselectivity (12 examples, up to >95:5 dr, >99:1 er). A matched-mismatched effect between the enantiomer of the catalyst and oxaziridine was identified, and preliminary mechanistic studies have allowed the proposal of a model to explain these observations. |
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Keywords: | Corresponding authors |
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